N-((4SR,1RS)-4-hydroxycyclohex-2-enyl)benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((4SR,1RS)-4-hydroxycyclohex-2-enyl)benzamide
• 英文别名: cis-4-(benzoylamino)cyclohex-2-enol；N-[(1S,4R)-4-hydroxycyclohex-2-en-1-yl]benzamide
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: YTAGQJZSGLWWBR-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((4SR,1RS)-4-hydroxycyclohex-2-enyl)benzamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以99%的产率得到cis-4-(benzoylamino)cyclohexanol
  参考文献：
  名称：

  Synthetic approaches to nortropanes and nortrop-6-enes; intramolecular displacement by nitrogen in 7-membered rings

  摘要：

  The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described. The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described. Nitrogen inversion data for selected nortropane derivatives are included.

  DOI：

  10.1016/s0040-4020(01)80313-6
• 作为产物：
  描述：

  苯甲羟肟酸 在 aluminum amalgam 、 tetramethylammonium metaperiodate 、 水 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 N-((4SR,1RS)-4-hydroxycyclohex-2-enyl)benzamide
  参考文献：
  名称：

  Synthetic approaches to nortropanes and nortrop-6-enes; intramolecular displacement by nitrogen in 7-membered rings

  摘要：

  The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described. The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described. Nitrogen inversion data for selected nortropane derivatives are included.

  DOI：

  10.1016/s0040-4020(01)80313-6

文献信息

• Reductive cleavage of NO bonds in hydroxylamines and hydroxamic acid derivatives using samarium diiodide
  作者：Gary E. Keck、Travis T. Wager、Stanton F. McHardy

  DOI：10.1016/s0040-4020(99)00486-x

  日期：1999.10

  An efficient process for the reductive cleavage of NO bonds using samarium diiodide is detailed for a variety of structural types to define the scope and limitations of the method. The reduction is shown to be compatible with base sensitive substrates such as trifluoroacetamide derivatives, which cannot be reduced satisfactorily using aluminum amalgam or sodium amalgam. Direct quenching of the reduction

  针对各种结构类型，详细介绍了使用二碘化sa还原N = O键的有效方法，以定义该方法的范围和局限性。还原显示与碱敏感的底物如三氟乙酰胺衍生物相容，使用铝汞齐或钠汞齐不能令人满意地还原。已证明用酰化剂直接淬灭还原混合物可在一锅法中由N = O衍生物提供高收率的受保护胺。
• Reductive cleavage of NO bonds in hydroxylamine and hydroxamic acid derivatives using SmI2/THF
  作者：Gary E. Keck、Stanton F. McHardy、Travis T. Wager

  DOI：10.1016/0040-4039(95)01557-4

  日期：1995.10

  The title reaction affords a general method for the reductive cleavage of NO bonds, and is successful in some cases where established methods fail.

  标题反应提供了还原NO键的一般方法，并且在某些已建立方法失败的情况下是成功的。
• New Preparation of Activated 2-Vinylaziridines from 1,4-Aminoalcohols
  作者：Horacio F. Olivo、Michael S. Hemenway、Amy C. Hartwig、Raymond Chan

  DOI：10.1055/s-1998-1635

  日期：1998.3

  Activated vinylaziridines (N-benzoyl, N-p-toluenesulfonyl, N-t-butoxycarbonyl and N-benzyloxycarbonyl) have been prepared from N-substituted 1,4-aminoalcohols using Mitsunobu conditions.

  活化乙烯基氮丙啶（N-苯甲酰基、N-对甲苯磺酰基、N-叔丁氧羰基和 N-苄氧羰基）是利用三忍条件从 N-取代的 1,4-氨基丙醇中制备出来的。
• Asymmetric diels - alder reactions with α-chloronitroso compounds - I. Application of α-chloronitroso epiandrosterone in synthesis
  作者：Mahmud Sabuni、Günter Kresze、Heinz Braun

  DOI：10.1016/s0040-4039(01)91288-2

  日期：1984.1

  The Diels - Alder reaction of 1,3-cyclohexadiene (9) with the enantiomerically pure α-chloronitroso compound 8, synthesized from epiandrosterone (7a), gives the adduct 10a with 1-(R),4-(S) configuration in 69 % chemical yield and ⩾95 % enantiomeric excess.

  1,3-环己二烯（9）与对映体纯的α-氯亚硝基化合物8（由表雄酮（7a）合成）的Diels-Alder反应在69中得到1-（R），4-（S）构型的加合物10a ％的化学收率和约95％的对映体过量。
• Mild Cleavage of N–O Bond of 3,6-Dihydro-1,2-oxazines by Condensation of Aldehydes in Aqueous Media
  作者：Cyrille Kouklovsky、Gilles Galvani、Robert Lett

  DOI：10.1055/s-0034-1380533

  日期：——

  The nonreductive cleavage of a model 3,6-dihydro-1,2-oxazine by condensation of 2,2-dimethoxyacetaldehyde under aqueous conditions is investigated. Depending on the pH of the solution, the reaction leads either to the N-acylated 1,4-amino alcohol or to the corresponding stable hemiaminal. The formation of the former is believed to proceed through iminium to oxaziridine rearrangement and not through enamine formation, as confirmed by the use of nonenolizable aldehydes. This procedure allows a very mild, nonreductive cleavage of N-O bonds.